]]>In 2011, I wondered how the increasing state of connectedness was going to impact us as people. How will it change how we interact with technology and how will a society that is data-informed evolve? Those questions prompted me to start the Roadmap conference — an idea which was slightly ambiguous, looking at the impact of connectedness on society. From Dropbox’s Drew Houston to Sequoia Capital’s Mike Moritz to Twitter’s Jack Dorsey — most of our speakers had spent a long time thinking about connectedness.

Roadmap 2011, a conversation between Om Malik and Jack Dorsey.

What emerged from the first edition of Roadmap was that design was the bridge that connected people and technology. Design was not just aesthetic beauty but more about creating continuous moments and experiences of joy by making technology productive. My long time colleague and creative partner, Katie Fehrenbacher joined as co-chair and together in the 2012 and 2013 editions of the event, we explored the evolution of design and its impact on our daily lives. From Tinder CEO Sean Rad to Instagram’s Kevin Systrom to font genius/giant Erik Spiekermann — everyone agreed that:

Those two core learnings led us to conclude about the invisibility of design — or invisible design — which is the core theme of Roadmap 2014. We have a stellar line up of speakers — too long to list. I am personally interviewing:

Our long list of all star speakers include Matias Duarte of Google, KK Barrett, production designer who has worked with Spike Jonze on films such as Her; Simon Rogers of Twitter, my dearest friend Elle Luna, Julie Zhuo of Facebook, Jessica Hische. And to cap them all, we will have John Maeda for a much-in-demand encore, where he will share his thoughts, especially how working in Silicon Valley has changed how he views design and its impact.

We have changed our location this year to the lovely and fantastic new SF Jazz Center — a venue where creativity is center stage every day of the year. On November 18 & 19 (and a kick off event on the night of November 17), we will bring forth a different aspect of creativity in technology. Katie & I hope you can join us — I know I would love to see you all at the conference. (You can click here to register.)

]]>The Walt Disney Company announced Monday that Square CEO and Twitter co-founder and chairman Jack Dorsey has been elected to the company’s Board of Directors. Dorsey will serve as “an independent director,” and stand at a meeting in March of next year.

Dorsey is not the only Silicon Valley face on Disney’s board — Facebook COO Sheryl Sanberg has been a board fixture since 2010. But it’s hard to not draw comparisons to another former Disney director and tech luminary, Steve Jobs. Jobs served on the board until his death in 2011, and his family still has a rather large stake in the company.

As one of America’s oldest brands, Disney could probably use an injection of fresh thinking around experience design, which Dorsey talked about at our Roadmap conference with Om Malik back in November:

]]>What does Jack Dorsey know about retail point-of-sale systems? That was the big question potential investors had for Square’s founder and CEO when he sought their funding five years ago, Dorsey said on stage at Gigaom’s RoadMap conference Tuesday.

“People would look at Square and they would say ‘your previous life was about micro-blogging what you had for breakfast,’” the Twitter co-founder said. “’Why do you think you can move money around? You’ve never worked in finance, you’ve never dealt with credit cards. Sellers aren’t the sexiest thing in the world.’ This was all their perception.”

At the time Dorsey didn’t have a definitive answer. In fact, he gave investors a lot of reasons why Square could fail, which probably cost Square a lot of interest from prominent VCs, Dorsey recalled.

But Dorsey has an answer now. Square’s engineers and designers may not be merchants or bankers. They may not have had much experience building the card readers and financial transaction networks that power plastic commerce, but they all were buyers of retail goods. According to Dorsey:

“We wanted to make something internally that we feel great about, that we feel is something that feels really amazing, that feels really stunning, that feels like something we want to use everyday. That was very, very hard in the early days of the company because a lot of us in the company — we’re not merchants, we’re not sellers. We’re not building for people who are us.

“When you’re building for yourself, it’s easy to have passion. It’s easy to have drive. But when you’re not, it becomes much, much harder. One of the framings that we got into was that we are all buyers. We love these merchants that we go to. We love these places like Blue Bottle and Sightglass Coffee. We want to do right by them. We want to have a great experience as well. We don’t want to have them wait and try to figure out an ugly point-of-sale system and all of these mechanical things, because that actually impacts the time that I spend in line or the time it takes to get the cappuccino that I just ordered.”

Square stepped back from the payment transaction and all of its component parts and approached commerce as an interaction between two people. It then sought to simplify that interaction as much as possible, Dorsey said. The result was Square Reader, but the company applied that same principle to its other products, from Square Stand and Market to its new peer-to-peer payments service Square Cash.

“It’s not about technology disappearing or how we design things, or how we engineer things,” Dorsey said. “This is what we want to use every single day, and we hope it resonates with other people. We’re making the bet it’s going to resonate with other people. We go out as far as we can, and we just work backwards. We break it into small problems. To me, a lot of what great engineering and design is, is taking something that is very large and very complex and breaking it into simple problems.”

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A transcription of the video follows on the next page

It was at a party, a few blocks from where I live and work — San Francisco’s South of Market neighborhood. I was hanging outside, sucking on a stogie, and chatting with Twitter’s forgotten co-creator, Noah Glass. I learned about Twitter (or Twttr as it was known then), played around with it on my Nokia E71 phone, went home, blogged about it and went to sleep. And just like that, the service that over 230 million people now use every month was announced to the public. And if anything, that original post is a lesson in humility; a reminder that no one knows what the future holds.

I was skeptical, but oddly addicted. I was cautious, and yet optimistic. I tried to define Twitter then, and failed. I have tried many times since, and failed. After all these years, I still have not been able to come up with one singular definition.

Some have called it a megaphone for the planet. Others like PayPal co-founder Max Levchin have compared it to talk radio. My friend Narendra Rocherolle, in a post for us (back when Twitter first launched,) compared it to tamagotchi. The best I can do is to compare it to the pulse of our planet, one that gives the internet a sense of humanity.

Of course, in the same breath you could turn around and label it the love child of Hank Moody (the lovable rascal who is the lead character of Californication) and Miley Cyrus — in other words a dysfunctional and narcissistic marketing platform; a theater that is always playing a “movie starring me.”

Twitter, at its very core, is many things to many people: that is its beauty and that is its challenge. Twitter the idea and the product is ever evolving, and so is the company, which was and still is a work in progress. I have had a courtside seat to this evolution and what I have learned is that Twitter is one of the most unique companies I have come across in my twenty-plus years of writing about technology, innovation and optimism.

I once compared Facebook to the Roman Army, relentless and ruthless in its pursuit to conquer it all. Nothing has changed my opinion of Mark Zuckerberg’s company. Twitter, on the other hand, always reminds me of that rag-tag group that blows up the dam at the end of Force 10 From Navarone. (I originally compared Twitter to a UN Force.)

Twitter is unique because it was born in the crucible of failure and grew up in the glare of the spotlight. It took from its community, it learned from its community and sometimes it did shameful things. It failed in the public eye — after all its fail whale icon once was a badge for technical incompetence.

But that comes with the territory. For a long time at Twitter, being open and social weren’t buzzwords. Despite disappointing some of us in the last few years, it has remained a remarkably transparent company. Recently, Twitter was mocked for experimenting with its news stream in public. I wouldn’t have it any other way. However, critical as I might be of the company at times, I like that some of the old Twitter DNA is still intact.

Twitter CEO Dick Costolo isn’t afraid to take to (what else) Twitter and joust with his detractors, distasteful as it might seem. New Twitter employees announce their glee at joining Twitter on Twitter, and those leaving the flock say their goodbyes publicly. And if you pay close attention to the twitter accounts of Twitter employees, you can pretty much put two and two together, and see what’s happening inside the company. Like I said, being open is not merely a buzzword. And that’s what makes it different.

The founders club

The co-creators of Twitter are just regular dudes who have demons much like our own. It is why we can relate to them. They seem so approachable — and they are — and their success is so personal. It is like watching someone play and cheering for them in the minor leagues only to suddenly find them playing in the major leagues. When we look at Twitter founders, we are reminded of that very feeling.

Mark Zuckerberg, Larry Page and Sergey Brin might be towards the top of the billionaire’s list, but they aren’t like Jack, Ev, Noah and Biz. They are not us — and that isn’t a bad thing.

When reading Nick Bilton’s tell-all book, Hatching Twitter, I saw that human frailty and all the baggage it drags along. In many ways, it is a story of anyone of us who are trying to figure out the future. Twitter is a reminder that successful startups start with a crazy dream, a random doodle (or a drunken conversation in Twitter’s case) that is then followed by a series of coincidences. Twitter is a random series of events posing as a corporation.

Yes: it is trying to become like Facebook in order to appease the demons of downtown Manhattan, who will soon be yanking its chain. But for now it is still the Twitter we know — flawed, fantastic, frustrating and it is the future. To me, it is a prototype of a company that was built on and for our interconnected planet. It is a company whose culture is defined less by its founders or by its chief executive but instead by those of us who use the service every day. It lives and dies in public. Let’s forget trying to to understand it, and forget trying to productize it. Twitter is us!

The uncertain future

The Twitter of today is facing an uncertain tomorrow. Uncertain, because a company that bows to Wall Street is bound to lose some of its folksy charm. You can see that already — many of the decisions being made by the company are being made to appease its investors; some are betting a successful Twitter offering will help them secure funds for their efforts to find the next Twitter.

Wall Street will take over from them, and will ask questions such as the amount of dollars that can be made per 1,000 tweets or something equally banal, like how many timelines can be monetized. Twitter is about to enter that weird zone where need for growth trumps everything, including one’s values.

That is Twitter’s fork in the road. Does is want to be like Google, a company with faint regard for Wall Street’s expectations, delivering growth and sticking to its original (if somewhat more evil) game plan? Or does Twitter want to follow the path of Facebook, which in the process of appeasing Wall Street has become a little more complex, a little more spangled with banners, a lot less social and much more draconian in its pursuit of data that can be used to attract advertisers and thus grow and grow. Irrespective of the path it chooses, there is no doubt that Twitter is going to change. Its new masters will want it to change.

Twitter, as we all know, thanks to its S-1 filing, has a growth problem — a problem that comes from the fact that average folks (like my mom) come to Twitter, scratch their heads and leave. (And that is why I don’t mind that Twitter is trying to be like Facebook, though clearly being Facebook isn’t working for Facebook either.) And if that is not enough, Twitter faces the challenge all aging consumer internet services eventually face — an audience that is aging with it.

The kids of today have other internet distractions and ways of spending their attention. Snapchat and Instagram have shown that visual is the medium of communication for generation mobile. Cracking the growth code, attracting younger audiences and evolving the product without alienating the current user base are pretty steep mountains to scale — especially hard to do when hired guns and not founders are running product.

So what about the IPO?

What about it? In my most recent appearance on Bloomberg TV, I told host Emily Chang that Twitter would have a much more normal offering than say Facebook. The company — thanks to its former CFO and current COO Ali Rowghani — has done a good job of laying out a clear, concise and simple storyline.

Dick Costolo is funny and disarming. Twitter’s ad chief Adam Bain is a great salesman. This is a team put together to sell the offering with minimum fuss. We have already seen the initial price range go up to around $25 a share, perhaps even higher and from the looks of it, and Twitter will go to market and stuff its coffers with about $2 billion. The company will have a long honeymoon period where Wall Street will adore whatever it says — as long as the sales keep growing. It has ad-matching technology that is starting to work. Given that now anyone (and that includes Twitter and brands) can send direct messages into your DM box without following you, don’t be surprised if you see Twitter launch some kind of direct marketing type advertising.

BTIG Research’s Rich Greenfield (a bull) believes that the company will have $1.1 billion in revenues in 2014, $1.75 billion in 2015 and by 2016 that number will grow to $2.7 billion. All this will eventually take a toll on the product experience because there isn’t a Zuckerberg-like founder to help figure things out: they are all busy with their next new things. Jack has Square. Ev has Medium. Biz has Jelly. Noah has Noah.

With no clear product leader, it might be best for Twitter management and Wall Street to embrace what I learned a long time ago: You have to let Twitter (the company) just be Twitter, an idea that evolves and morphs with the times and for those who love it.

I say the deal is important because Staples puts Square front in center before the small businesses that routinely use its website and physical stores to buy their office supplies, equipment and technology. While its previous distribution deals with Apple and Best Buy showcase Stand’s capabilities and design to a broad audience, Staples is all business. Staples is already a distributor for Square Reader, the smartphone-mounted credit card swiper that drove Square’s initial volumetric growth.

Though Stand is still new – going on sale only this past July – Square claims it’s already proving to be a much different animal than Reader. While the smartphone-payments gadget attracted a more mobile set of small businesses, Stand is appealing to larger businesses with physical storefronts and larger transaction volumes such as grocery stores and restaurants. Though Square isn’t revealing how many Stands it has sold so far, it said today that 70 percent of the businesses purchasing the system are either entirely new to Square or have never used Reader on a regular basis.

In a recent interview, Square’s head of hardware Jesse Dorogusker told me that Square is trying to re-envision the entire retail sales counter experience, starting with Stand. Dorogusker considers the mess of point-of-sale contraptions that typically overflow a sales counter to be a tremendous eyesore that distracts both the buyer and seller from what should be a more human transaction. “I’m about to hand over my hard-earned money, and I have to peer around this enormous ugly tower,” Dorogusker said.

While Stand is the centerpiece to Square’s concept of a more human sales counter, it’s not the only component. While Square doesn’t have any immediate plans to build its own receipt printers, barcode scanners or cash drawers, Dorogusker said it is working closely with other point-of-sale device makers to integrate more subtly designed and streamlined peripherals with Stand through USB, Ethernet and Wi-Fi. It’s already done that integration with specific peripherals from APG, Symbol and Star Micronics.

“We want to build everything,” Dorogusker said. “Of course, you have to pick and choose the things you can build.”

Square is taking a similar approach to online commerce with its new Market, which gives small businesses mobile and web sales tools, just as Stand gives them more in-store sales flexibility. Square founder and CEO Jack Dorsey will have plenty more to say on how his company is trying to reshape retail commerce through design at Gigaom’s RoadMap conference on Wednesday. If you’re not attending, you can watch the free livestream on Gigaom’s website.

Square said iPad-equipped Stands will be set up at several Staples locations so customers can try out the terminal interface and the Register app that powers it. Staples and Square are also sweetening the pot for customers who buy Stand in November either online or at the store, offering a $200 rebate in the form of a Visa prepaid card or Staples gift card, effectively cutting Stand’s normal $300 price tag by two thirds.

]]>Square Market launched as a means for Square’s small business sellers to quickly establish and online storefront and easily promote their goods with social media tools, but Market is showing signs of evolving into an independent online marketplace, competing with the likes of Etsy and Fab.

According to Ajit Varma, who heads up Market for Square, 20 percent of Square’s 500,000 listed merchants have never used its payments hardware, Reader and Stand – they’re solely selling and marketing online. The distinction between selling and marketing is important because only about 50,000 Market merchants are actually selling their goods online.

Instead, most Square merchants use Market to establish an online and mobile presence – a place to display their goods, services and pricing. For instance, neighborhood grocery stores are using Market to list their beer inventories and current prices with the aim of attracting locals to its store. Most of those retailers use Square payments technology at the physical point of sale, but as Varma pointed out, an increasing number are not. They’re only using Square online, some for e-commerce (Square is charging the same 2.75 percent transaction fee as it does for a Reader swipe) but others merely as a marketing tool.

Since Square doesn’t charge merchants to set up shop and list items in Market, it isn’t collecting any online revenue from the most of these merchants, so why bother with Market at all? A lot of it has to do with Square’s philosophy of taking the complexity of payment transactions and designing simple yet well-designed commerce products that all relate to one another – a philosophy that Square CEO Jack Dorsey will discuss in more detail at Gigaom’s Roadmap conference next week.

Varma explained that as Square’s core merchant base expands from small mobile business owners working in the field to larger retail businesses such as stores and restaurants, the company has had to expand its portfolio of commerce tools. That was the logic behind Stand, which is Square’s more sophisticated counter-top payments terminal. And that’s the same logic behind Market, Varma said, except extending beyond the physical point of sale onto the internet.

“Square is growing [to support] these larger merchants,” Varma said. “A lot of these larger merchants don’t know how to participate in the online economy.”

While many sellers might have their own webpages or a Facebook profile, most of them haven’t invested that much into web development. Market not only gives them the tools to set up simple yet artfully designed online storefronts in the PC browser, but also on the mobile browser, which is becoming increasingly important. More than 40 percent of Market’s traffic is coming from mobile devices, Varma said.

Market also gives them social media tools to promote their goods – for instance product cards to highlight a sale item in a Twitter feed. As with all of its Square’s merchant products, Market links back Square’s central dashboard, allowing businesses to manage their inventories and pricing across both online and physical stores. Meanwhile its analytics engine helps retailers identify both overall and in-store trends, which in turn can be tied back to Square’s social marketing tools.

Different businesses use a combination of different transaction methods, so the idea is to let them tailor their commerce model using Square’s different products. For instance both a boutique store and a custom furniture maker might use Stand or Reader to process in-store transactions, but only the boutique would use Market for sales. The furniture maker would just use Market as way to display and promote its ottomans and divans online. Conversely a retailer that deals solely online would have plenty of use of Market, but little use for its hardware.

Square benefits from Market because it’s generating more transactions, either directly or indirectly. While Market helps generate more transactions for Square’s existing merchants, Varma said, it’s also broadening its appeal among different types of sellers and putting many more buyers in front of those merchants. Varma’s last point is particularly telling: Half of all payments processed so far on Market have come consumers who have never made a Square payment before.

]]>I have re-kindled my love affair with fountain pens and as a result, there have been a few new additions to my collection of writing instruments. And given that some are relatively expensive, I decided to order a pen case from a small leather goods maker in North Carolina. It was well priced, and reviews indicated that it was well made. Their website was clean, simple and kept the focus on the goods.

However, when it came time to pay for the pen case, I was taken to PayPal’s website — and that is when the experience of interacting with the brand was broken — not because they (the pen case maker) did anything wrong, it was just that the PayPal interface and the user experience was so different from them. The checkout page acted like a time machine, taking me back at least a decade, as if all the progress we have made with e-commerce didn’t really happen. As I proceeded to pay, I was faced with the friction of the PayPal experience.

That prompted me to ask: why doesn’t the pen vendor just take Square. I mean, all I have to do is send them an email and send them Square Cash, a new product that launched last week. I have been using the service for about a week and let’s just say that sending money (in the US) hasn’t ever been this easy before. (My colleague Kevin Fitchard, explains how it works in his piece on Square Cash.)

And while Square might not be as big as PayPal (yet), it has done one thing right: built a seamless experience. As somewhat of an ardent user of Square, I can appreciate a lot of invisible little things like the auto check-in on their Wallet app, the colors of cash sent or received (via Square Cash) or simply the clean, crisp emailed receipt. There is a consistency of experience: an expectation of payment being invisible and painless.

These days, when there is talk of design, most people focus on what they can see: the pretty websites, well designed gadgets and brilliantly colored packaging. And while those are important, what matters most to the customers is the whole experience. That experience is essentially a story, a narrative which ultimately enjoins us to a brand.

Designing this experience is what makes one company different from another. That is why experience design, which is the theme of our RoadMap Conference (November 5 & 6th, 2013 in San Francisco) has to be unique and can’t really be xeroxed. Square CEO and co-founder Jack Dorsey will be talking with me at RoadMap about how to create that experience.

It’s not an easy task. Microsoft did a good job of copying Apple stores, but it still lacks that seamless story, one that creates an experience like Apple. And the reason is not that Microsoft is making bad products — they are just making different things and have not been able to figure out what is their story and what is the experience they want to offer.

A perfect embodiment of a great experience design is Virgin America, an airline whose story can be told as “hassle free and happy travel.” That thesis is what they extend to the colors and interior lighting of their planes, and most importantly how they interact with their users. They are collaborative, friendly and playful and that is reflected in every single touch point users have with Virgin America. Virgin presents a sharp contrast to airlines like United and American — who undertook a major makeover, but no amount of paint can hide the fact that they have been unable to craft a consumer friendly experience, something I noted in an earlier post.

Airbnb uses Disney’s “Snow White” as a humanizing Service Design narrative framework in order to better understand and empathize with guests and hosts for the end to end experience. Since Airbnb’s product is the trip, it requires understanding and empathizing with guests and hosts, throughout the end-to-end experience.

Airbnb co-founder Joe Gebbia (who is speaking at RoadMap) is a designer who hails from the Rhode Island School of Design. He says designing a strong story and brand comes from paying attention to all those the little details that make up the whole experience for users. He encourages his design-centric team to celebrate and engage with all the little details. He once brought his entire product team to Jiro Dreams of Sushi as a way to point out excellence in detail-orience.

Airbnb has a unique challenge and opportunity when it comes to creating its experience that is different than building gadgets or re-branding airlines or launching payment systems. The relationship between host and user is an entirely new form of interaction — is it a hotel, a sublet, a friend’s couch? It is all of these things and also none of them. Thus the experience can be free of the legacies of the past, but needs more crafting than the legacy systems that it’s disrupting.

The newest and most interesting e-commerce brands are carefully crafting an end-to-end emotional experience to win over customers. Warby Parker paved the way with hipster frames, cheap prices and easy shipping, and now sites focused on selling women’s apparel like Gilt, Everlane, Wanelo, and True&Co are using data to rethink the e-commerce experience.

Data will no doubt play a crucial role in learning and reshaping the next-generation of connected experiences. Dennis Miloseski, the head of Samsung’s new year-old Design America studio in San Francisco, told us recently that Samsung troves research, data, analytics and ethnographic studies to try to get the experience of all its products just right. It might not always succeed, but it’s now turning to the design and data-centric approach of the Bay Area studio to help inform all of its divisions back in Korea.

Whether we talk about greeting cards, mobile apps, or vacation get-aways, the experience is the product. From the perspective of customers, everything that goes into making up that experience—technology, materials, service support, or a supply chain—simply becomes the magic behind the experience.

Yet the orientation and focus of our businesses is the inverse of this customer perspective. We plan around features and operational functions, leaving the customer experience as an unintentional byproduct of how the pieces and parts happen to come together for the customer.

During the heyday of the industrial and manufacturing economy, what mattered was the brand, Schauer says. Today, because we as a country are becoming essentially a services economy, the focus should be around the branded experience instead.

Square, for me is that type of experience. I am probably not going to remember what font is being used or what color type is on display. What I will remember is a process of easy cash exchange, whether it is with friends, family, my local butcher or cafe or Starbucks. That is the essence of a modern company — technology, infrastructure and complexity hidden by a well designed experience — that to me is experience design.

A personal message: Experience design is a new way of thinking about the world, and we will discuss this thinking at our RoadMap conference on November 5th and 6th in San Francisco where speakers from companies such as Square, Airbnb, True & Co., will tell us what works, and what doesn’t. I hope you guys can join me and Katie Fehrenbacher at the event.

And now a personal message: I am hosting GigaOM RoadMap, a one of its kind experience design conference with Katie Fehrenbacher on November 5th and 6th in San Francisco. I would love for you to join the two of us and we’ll have experts like Jack Dorsey (of Square and Twitter) and Kevin Systrom along with many more speakers tell us the role of design in our increasingly digital society. For details, visit the conference website.

]]>The New Yorker has published a long, languid look at the entrepreneurial talents of Twitter and Square creator Jack Dorsey, following him from an upstart college dropout in the ’90s to single-minded entrepreneur and now as a tailored veteran businessman and anticipated IPO beneficiary. While author D.T. Max presents Dorsey as a sort of restrained, introspective pseudo-Steve Jobs, there’s also plenty of talk surrounding the CEO’s “right place, right time” luck. But it establishes Dorsey as a figure in the pantheon of Silicon Valley greats, and remains optimistic for his next venture.

]]>It was an unusually busy week, mostly because of the preparations for our Mobilize conference next week. In addition, there were many events to be attended. Not surprisingly, all that activity ate into my reading time. But still, I did get enough time to put together this list, though I wish I had even more topic variety.

When a crop becomes king: Best selling author Michael Pollan on corn. This is a vintage article — from 2002 and it is a great read, because I have always been fascinated by corn and the role it plays in modern society.

Modern Miners: The genomic gold rush: The title says it all, but in case you were wondering this is a piece that explores the opportunities that are opening up with the decoding of genome and the cloud.

And now a personal message: I am hosting GigaOM RoadMap, an experience design conference with Katie Fehrenbacher on November 5th and 6th in San Francisco. I would love for you to join the two of us and we’ll have experts like Jack Dorsey (of Square and Twitter) and Kevin Systrom along with many more speakers tell us the role of design in our increasingly digital society. For details, visit the conference website.